Head Outdoors to Learn to Lead

When I began in commercial real estate 25 years ago, the prevailing paradigm for young bucks was that of the “Man in Full.” Wall Street was the hot thriller and discussions about ethics in business were abound. To be an American male in business meant you had a streak of rugged individualism.

It’s seems ironic to me that this is changing in the world of commercial real estate, in that the real estate entrepreneur today is one who understands teamwork. This esprit de corps I learned when I was 16 years old at NOLS.

NOLS stands for the National Outdoor Leadership School, a nonprofit outdoor education school founded in 1965 and based in Wyoming.  My wife, Leslie,  spent 3 months in Alaska with the program and my brother, Ewell, and son, Mac, are alums as well.

NOLS’ mission is to help one step forward boldly as a leader.

Training is done in the classrooms of remote wilderness areas as far away as India, Patagonia, Scandinavia and the Yukon.

I did my first course when I was 16. It was a 30-day mountaineering trip in the forest and glaciers of the northern Cascades mountain range. Full of machismo and wearing a 90-pound pack, I was confident the trip would be a breeze for me. I was the biggest guy in the group and just finished a season of high school football. No problem, I thought, as I heaved on my pack and set out with 17 others ranging in age from 16 to 30, male and female, city dwellers and rural kids.

It will probably be no surprise for you to hear that the trip was not as easy as I’d naively thought it would be.

These are hard-ass trips designed to force people to learn how to function under difficult circumstances and make informed, thoughtful decisions while acting with confidence and competence. I haven’t found another situation where young people are given such real responsibilities – for themselves and to other people.

Netflix co-founder and Chair of the NOLS Board of Trustees Marc Randolph has credited the program with helping him build the grit to successfully lead. He’s a big proponent of the outdoors being an amazing teacher.  He has said straight up that NOLS is responsible for almost all of the professional accomplishments that he has made, and that he owes the school a huge debt for teaching him the skills to be successful as an entrepreneur.

As Randolph has written, NOLS isn’t just wilderness skills, it’s a leadership school where young people have to make decisions, clearly communicate them, and find out shortly whether they were good or bad ones.

Uncertainty is inevitable. As leaders, we are always having to make decisions based on what we know, with incomplete or even contradictory information. A NOLS course teaches one how to do that, and gives a person the chance to practice this skill over and over. That’s partially how one becomes a strong leader, with practice.

Back to the overly confident 16-year-old kid.  I made some dumb decisions. Early in the trip I got my boots – my only pair of boots – too close to the fire and burned the soles off. I spent the rest of the 20 days hiking in boots with the sole flapping away, separating from my boot. It was annoying and uncomfortable.

During the trip, I burned through my food and my fat cells and carbohydrates. I lost weight and was wiped out.  Meanwhile, I quickly learned that the girls in the group, smaller and less muscular, were the powerhouses and in there for the long haul. At the end of the trip, the guys were done, exhausted. The girls, meanwhile, were chipper and upbeat.

In addition to learning to recognize, and build on, my limitations, I came away with some leadership traits I incorporate in my daily life. They are:

  • Demonstrate good expedition behavior—take initiative, balance group and personal goals, and remain respectful and inclusive of all team members
  • Serve a team in a variety of roles: self leader, peer leader, designated leader, and active follower
  • Display a tolerance for adversity and uncertainty
  • Demonstrate self awareness
  • Display initiative by setting and achieving goals

The trip was grueling and ultimately invaluable. I encourage everyone to get outside and test themselves.

Find out more about NOLS at       


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